4887-88-1

Basic information

• Product Name: 5-Bromo-1H-benzimidazole
• Synonyms: 5-BROMO-1H-BENZIMIDAZOLE;5-BROMO-1H-BENZO[D]IMIDAZOLE;5-BROMO-1H-BENZOIMIDAZOLE;1H-Benzimidazole,5-bromo-(9CI);5-BROMOBENZIMIDAZOLE;6-bromo-1H-benzo[d]imidazole;6-bromo-1H-benzimidazole(SALTDATA: FREE);1H-BenziMidazole, 6-broMo-
• CAS NO: 4887-88-1
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• Product Categories: BENZIMIDAZOLE;pharmacetical;Imidazol&Benzimidazole;Building Blocks;C3 to C8;Chemical Synthesis;Heterocyclic Building Blocks;Imidazoles;New Products for Chemical Synthesis;Pharm intermediate
• Mol File: 4887-88-1.mol
• Article Data: 44

Chemical Properties

• Melting Point: 130 °C
• Boiling Point: 417.353 °C at 760 mmHg
• Flash Point: 206.208 °C
• Appearance: /
• Density: 1.771 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 11.19±0.30(Predicted)
• CAS DataBase Reference: 5-Bromo-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1H-benzimidazole(4887-88-1)
• EPA Substance Registry System: 5-Bromo-1H-benzimidazole(4887-88-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-36-22
• Safety Statements: 22-26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 4887-88-1(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

InChI:InChI=1/C7H5BrN2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,(H,9,10)

Synthetic route

formic acid (64-18-6) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
at 100℃;	100%
With hydrogenchloride In water for 3h; Reflux;	97.5%
for 2h; Reflux;	85%
With hydrogenchloride
Stage #1: formic acid; 4-Bromo-benzene-1,2-diamine for 2h; Reflux; Stage #2: With sodium hydroxide In water at 20℃;

4-Bromo-benzene-1,2-diamine (1575-37-7) + trimethyl orthoformate (149-73-5) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
Stage #1: 4-Bromo-benzene-1,2-diamine; trimethyl orthoformate With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide pH=7;	100%
With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;	100%
With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;	100%
With formic acid at 80℃; for 16h;

formic acid (64-18-6) + 4-bromo-1,2-dinitrobenzene (610-38-8) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With gold nano particles supported on rutile TiO2 In toluene at 70℃; under 750.075 Torr; for 6h; Inert atmosphere; chemoselective reaction;	96%

orthoformic acid triethyl ester (122-51-0) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With zirconium(IV) chloride In methanol at 20℃; for 3h;	95%
at 125℃;	79%
formic acid at 80℃; for 18h;

carbon dioxide (124-38-9) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With 4-dimethylamino-benzaldehyde In 1-methyl-pyrrolidin-2-one at 120℃; under 7500.75 Torr; for 24h; Flow reactor;	91%
With bis[1,2-bis(diphenylphosphine)ethane]ruthenium dichloride; hydrogen at 120℃; under 112511 Torr; for 40h; Green chemistry;	90%

5-bromo-2-mercaptobenzimidazole (68468-39-3) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With rose bengal; water; oxygen; sodium chloride In N,N-dimethyl-formamide at 25℃; for 48h; Irradiation; Green chemistry;	90%

Aminoiminomethanesulfinic acid (1758-73-2) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
In water at 60℃; for 1h;	89%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With Imidazole hydrochloride at 120℃; for 6h;	88%
With Triethoxysilane; carbon dioxide; tris(pentafluorophenyl)borate at 120℃; for 24h;	94 %Spectr.

carbon dioxide (124-38-9) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1-methyl-1H-benzo[d]imidazole (53484-15-4) + 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With phenylsilane at 50℃; under 22502.3 Torr; for 3h; Pressure; Autoclave;	A 7% B 88%

oxalic acid (144-62-7) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
In 1,4-dioxane at 120℃; for 6h; Green chemistry;	85%

methanol (67-56-1) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With potassium tert-butylate In 1,4-dioxane at 130℃; for 48h; Autoclave;	85%

formic acid (64-18-6) + 4-Bromo-2-nitroaniline (875-51-4) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With iron; ammonium chloride In isopropyl alcohol at 80℃; Inert atmosphere; Schlenk technique;	85%
With iron; ammonium chloride In isopropyl alcohol at 80℃; for 3h; Inert atmosphere;	82%

D-Glucose (2280-44-6) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With tert.-butylhydroperoxide; trifluorormethanesulfonic acid; water at 100℃; for 1h; Sealed tube;	81%

benzoimidazole (51-17-2) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 3h;	77%

4-Bromo-2-nitroaniline (875-51-4) + Aminoiminomethanesulfinic acid (1758-73-2) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 70℃; for 1.5h; Green chemistry;	68%

dimethyl sulfoxide (67-68-5) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
With ammonium acetate; water at 140℃; for 10h; Inert atmosphere; Schlenk technique;	67%

formaldehyd (50-00-0) + 4-bromo-phenylene-diamine-(1.2) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

formic acid (64-18-6) + 4-Bromo-benzene-1,2-diamine (1575-37-7) + trimethyl orthoformate (149-73-5) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
at 80℃; for 16h;

4-Bromo-2-nitroaniline (875-51-4) → 5-bromo-1H-benzo[d]imidazole (4887-88-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / H2NNH2; FeCl3*6H2O / methanol 2: 79 percent / 125 °C View Scheme

2-phenoxy-1-phenylethanone (721-04-0) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 5-bromo-2-phenyl-1H-benzo[d]imidazole (1741-50-0) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) + phenol (108-95-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 2-methoxy-ethanol at 120℃; for 24h; Sealed tube;

3,4-dihydro-2H-pyran (110-87-2) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole (1214899-89-4)

Conditions	Yield
With toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 18h; Inert atmosphere;	100%
With toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 18h; Inert atmosphere;	100%
With C21H17F3N6O2*C7H8O3S In tetrahydrofuran at 60℃;

di-tert-butyl dicarbonate (24424-99-5) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → 1,1-dimethylethyl 5-bromo-1H-benzimidazole-1-carboxylate (942590-05-8)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;	98%
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;	98%
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;	98%

5-bromo-1H-benzo[d]imidazole (4887-88-1) + pinacol vinylboronate (75927-49-0) + cyclopropylboronic acid (411235-57-9) → 1-cyclopropyl-5-vinylbenzimidazole + 1-cyclopropyl-6-vinylbenzimidazole

Conditions	Yield
Stage #1: 5-bromo-1H-benzo[d]imidazole; cyclopropylboronic acid With [2,2]bipyridinyl; copper diacetate; sodium carbonate In 1,2-dichloro-ethane at 80℃; under 775.743 Torr; for 48h; Stage #2: pinacol vinylboronate With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 16h;	A 85.79% B 85.79%

5-bromo-1H-benzo[d]imidazole (4887-88-1) + p-methoxybenzyl chloride (824-94-2) → 5-bromo-1-(4-methoxybenzyl)-1H-benzo[d]imidazole

Conditions	Yield
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride In tetrahydrofuran at 60℃; for 3h; Temperature;	78%

5-bromo-1H-benzo[d]imidazole (4887-88-1) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazole (444103-78-0)

Conditions	Yield
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In N,N-dimethyl-formamide Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide	77%
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 25℃; for 4h;	75%
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;	44%
Stage #1: 5-bromo-1H-benzo[d]imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil for 1h; Inert atmosphere;	44%

5-bromo-1H-benzo[d]imidazole (4887-88-1) + C11H13NO4S → C18H18BrN3O4S

Conditions	Yield
Stage #1: 5-bromo-1H-benzo[d]imidazole With potassium carbonate In acetonitrile at 50℃; for 0.666667h; Stage #2: C11H13NO4S In acetonitrile at 75℃;	73%

5-bromo-1H-benzo[d]imidazole (4887-88-1) + C11H13NO4S → C18H18BrN3O4S

Conditions	Yield
Stage #1: 5-bromo-1H-benzo[d]imidazole With potassium carbonate In acetonitrile at 70℃; for 0.5h; Stage #2: C11H13NO4S In acetonitrile at 20 - 70℃;	72.8%

carbon dioxide (124-38-9) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → 5-benzimidazolecarboxylic acid (15788-16-6)

Conditions	Yield
Stage #1: 5-bromo-1H-benzo[d]imidazole With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Stage #3: carbon dioxide In tetrahydrofuran; hexane at -20℃; for 0.5h;	71%

2-nitrophenylboronic acid (5570-19-4) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → 5-(2-nitrophenyl)-1H-benzo[d]imidazole

Conditions	Yield
In water	66%

benzyl (2,2-dimethylbut-3-ynoyl)-L-leucyl-L-valyl-L-phenylalaninate + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → benzyl (2-(1-(1H-benzo[d]imidazol-5-yl)-1H-1,2,3-triazol-4-yl)-2-methylpropanoyl)-L-leucyl-L-valyl-L-phenylalaninate

Conditions	Yield
With copper(l) iodide; sodium azide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium L-ascorbate In water; dimethyl sulfoxide at 70℃; for 4h; Inert atmosphere;	66%

2-nitrophenylboronic acid (5570-19-4) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → [2-(1H-1,3-benzodiazol-5-yl)phenyl]azinic acid

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 40 - 80℃; for 12h; Inert atmosphere;	66%

5-bromo-1H-benzo[d]imidazole (4887-88-1) → 5-bromo-4,6,7-triiodo-1H-benzimidazole (1196457-08-5)

Conditions	Yield
With sulfuric acid; iodine; periodic acid at 60℃; Cooling with ice;	65%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 5-bromo-1H-benzo[d]imidazole (4887-88-1) → 6-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole (1299292-27-5) + 5-bromo-1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)benzimidazole (1299292-26-4)

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 3h; Reflux;	A 36% B 61%
Stage #1: 5-bromo-1H-benzo[d]imidazole With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane for 24h; Reflux; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 2h; Reflux;	A 29% B 24%

Upstream product

• 64-18-6 formic acid 
• 1575-37-7 4-Bromo-benzene-1,2-diamine 
• 50-00-0 formaldehyd 
• 610-38-8 4-bromo-1,2-dinitrobenzene 
• 1758-73-2 Aminoiminomethanesulfinic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 875-51-4 4-Bromo-2-nitroaniline 
• 149-73-5 trimethyl orthoformate 
• 51-17-2 benzoimidazole 
• 122-51-0 orthoformic acid triethyl ester 
• 67-56-1 methanol 
• 5228-61-5 5-bromo-2-nitroaniline 
• 67-68-5 dimethyl sulfoxide 
• 144-62-7 oxalic acid 

Downstream Products

• 942590-05-8 1,1-dimethylethyl 5-bromo-1H-benzimidazole-1-carboxylate 
• 1006899-77-9 tert-butyl 6-bromo-1H-benzo[d]imidazole-1-carboxylate 
• 1248590-91-1 4-((1H-benzo[d]imidazol-6-yl)(methyl)amino)benzonitrile 
• 1248590-89-7 1-(4-((1H-benzo[d]imidazol-6-yl)(methyl)amino)phenyl)ethanone 
• 1248590-90-0 1-(1H-benzo[d]imidazol-6-yl)-4-phenylpiperidine-4-carbonitrile 
• 5918-91-2 (1⁽³⁾H-benzoimidazol-5-yl)-(4-methoxy-benzyl)-amine 
• 1342887-11-9 N-(4-Fluorobenzyl)-3H-benzo[d]imidazol-5-amine 
• 1342887-08-4 N-(4-Chlorobenzyl)-3H-benzo[d]imidazol-5-amine 
• 1342887-10-8 N-(4-Methylbenzyl)-3H-benzo[d]imidazol-5-amine 
• 1342887-12-0 N,N-dibenzyl-1H-benzo[d]imidazol-5-amine 
• 5918-89-8 N-benzyl-1H-benzo[d]imidazol-5-amine 
• 1342887-07-3 N-(3,4-Dimethoxybenzyl)-3H-benzo[d]imidazol-5-amine 
• 1342887-09-5 N-(1-Phenylethyl)-3H-benzo[d]imidazol-5-amine 
• 1342887-06-2 N-Phenethyl-1H-benzo[d]imidazol-5-amine 

Relevant articles and documents

Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles

We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc

Method for synthesizing benzimidazole from carbon dioxide and o-phenylenediamine compound

The invention discloses a method for synthesizing benzimidazole from carbon dioxide and an o-phenylenediamine compound, the method is characterized in that an amino-containing functionalized ordered mesoporous polymer is used as a catalyst, o-phenylenediamine and carbon dioxide are used as raw materials, dimethylaminoborane is used as a hydrogen reduction reagent, carbon dioxide and the o-phenylenediamine compound are catalyzed to react in an NMP solvent to generate a benzimidazole compound, wherein the dosage of a catalyst is 0.01-1mol% based on the nitrogen content of the o-phenylenediamine compound; the filling pressure of the carbon dioxide is 0.1-2MPa; the reaction temperature is 60-180DEG C; the molar ratio of the catalyst to the NMP is 1:50-100. Compared with the prior art, the catalyst has the advantages of simple preparation, high catalytic activity, capability of catalyzing the reaction of carbon dioxide and the o-phenylenediamine compound under mild conditions to generate benzimidazole and derivatives thereof, and the like.

Sustainable Synthesis of 2-Hydroxymethylbenzimidazoles using D-Fructose as a C2 Synthon

D-fructose, a biomass-derived carbohydrate has been identified as an environmentally benign C2 synthon in the preparation of synthetically useful 2-hydroxymethylbenzimidazole derivatives by coupling with 1,2-phenylenediamines. Proof of concept was established by synthesizing 23 examples using BF3.OEt2 (20 mol%), TBHP (5.5 M, decane) (1.0 equiv.) in CH3CN at 90 °C for 1 h. The pivotal features of this method include metal-free conditions, short time, good functional group tolerance, gram scale feasibility and the synthesis of benzimidazole fused 1,4-oxazine. Control studies with conventional C2 synthons did not produce the desired product, thus suggesting a new reaction pathway from D-fructose.